Issue 1, 2016

2-(Anthracenyl)-4,5-bis(2,5-dimethyl(3-thienyl))-1H-imidazole: regulatable stacking structures, reversible grinding- and heating-induced emission switching, and solid-state photodimerization behavior

Abstract

2-(Anthracenyl)-4,5-bis(2,5-dimethyl(3-thienyl))-1H-imidazole (anbdtiH) has been synthesized. Its three solid-state structures, anbdtiH·CH3Cl (1), anbdtiH·2CH3OH (2) and anbdtiH2·CF3COO·CH3OH·H2O (3), have been constructed by skillfully choosing CHCl3 or CH3OH as the solvent and using or not using CF3COOH, with the aim of modifying the intermolecular hydrogen bonds and/or π⋯π stacking interactions. The three distinct structures show significantly different solid-state luminescence behaviors, an orange-red emission at 603 nm for 1, a blue emission at 453 nm for 2, and a green emission at 533 nm for 3. Upon grinding, these emission wavelengths exhibit evident variations, a blue-shift of Δλ = 83 nm for 1, a red-shift of Δλ = 20 nm for 2, and a blue-shift of Δλ = 54 nm for 3. The emission color of 1 can be reversibly switched between orange-red and green upon regulation of the intermolecular (N–H)imidazole⋯Nimidazole hydrogen bonds by a grinding–heating process. Moreover, compound 3 can undergo a solid-state [4π + 4π] photodimerization reaction upon irradiation with sunlight, forming 3-dimer. Based on the crystal structures of 1–3, this work discusses the relationship between the molecular stacking mode and the luminescence behavior/photochemical reactivity.

Graphical abstract: 2-(Anthracenyl)-4,5-bis(2,5-dimethyl(3-thienyl))-1H-imidazole: regulatable stacking structures, reversible grinding- and heating-induced emission switching, and solid-state photodimerization behavior

Supplementary files

Article information

Article type
Edge Article
Submitted
27 ago 2015
Accepted
07 out 2015
First published
08 out 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2016,7, 451-456

2-(Anthracenyl)-4,5-bis(2,5-dimethyl(3-thienyl))-1H-imidazole: regulatable stacking structures, reversible grinding- and heating-induced emission switching, and solid-state photodimerization behavior

J. Chen, D. Gong, J. Wen, H. Ma and D. Cao, Chem. Sci., 2016, 7, 451 DOI: 10.1039/C5SC03201F

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